8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acid → 7-fluoro-8-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid

HRID 465007Notes

Reaction equation

HRID 465007 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:19].[CH2:20]([NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)[CH3:21]>N1C=CC=CC=1>[F:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:26]1[CH2:27][CH2:28][CH:24]([CH2:23][NH:22][CH2:20][CH3:21])[CH2:25]1)[N:9]1[CH2:12][CH2:13][S:14][C:8]1=[C:7]([C:15]([OH:17])=[O:16])[C:6]2=[O:18]

Participants

4

Reactant 2

HCID 104700458-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acidHCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

Product 1

HCID 202614477-fluoro-8-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3.0 g (10 mmol) of 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid, 1.93 g (15 mmol) of N-ethyl-3-pyrrolidinemethanamine and 50 ml of pyridine is heated at reflux for 18 hours. The solvent is removed in vacuo and the residue triturated with water. The solid which separates is removed by filtration, washed with water and dried in vacuo to give 7-fluoro-8-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-5-oxo-1,2-dihydro-5H-thiazolo[3,2-a]quinoline-4-carboxylic acid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent is removed in vacuo
  4. customthe residue triturated with water
  5. customThe solid which separates is removed by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-714fa2fec0c646b28375708d367ac84d
Source dataset
uspto-grants-1985_10
Patent number
US04550104

Reaction notes

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